6,6A,7,11B-Tetrahydro-5H-indeno(2,1-C)isoquinoline hydrochloride

ABSTRACT

The title compound is a useful anthelmintic agent.

United States Patent [191 Schwan Nov. 18, 1975 I 6,6A,7,llB-TETRAHYDRO-SH-INDENO(2,1-

C )ISOQUINOLINE HYDROCHLORIDE [75] Inventor: Thomas J. Schwan, Norwich, NY.

[73] Assignee: Morton-Norwich Products, Inc., Norwich, NY.

[22] Filed: Sept. 16, 1974 [21] Appl. No.: 506,295

[56] References Cited UNITED STATES PATENTS 3,830,647 8/1974 Janssens 260/283 R OTHER PUBLICATIONS Govindachari et. al., Chem. Ber., 91, 2053-2060, (1958).

Primary ExaminerDonald G. Daus Assistant Examiner-David E. Wheeler Attorney, Agent, or Firm--Anthony J. Franze [57] ABSTRACT The title compound is a useful anthelmintic agent.

1 Claim, No Drawings 6,6A,7,l lB-TETRAHYDRO-SH-INDENO(2,l- C )ISOQUINOLINE HYDROCHLORIDE This invention is concerned with the chemical compound 6,6a,7,l1b-tetrahydro-5H-indeno[ 2,1- clisoquinoline hydrochloride. It is useful as an anthelmintic agent. When administered per by gavage in a suspension at a dose of about 100 mg/kg to mice harboring the pinworm Syphacia obvelata, a 90 percent reduction of pinworm population is secured.

The method currently preferred for the preparation of the compound of this invention is briefly described as follows:

A. Z-Benzylamino-l-indanol Hydrochloride Tetartohydrate A mixture containing 55.8 g (0.262 mole) of 2- bromo-l-indanol and 56.0 g (0.524 mole) of benzylamine in 250 ml dioxane was stirred and refluxed for 4 days, cooled and stirred at ambient temperature for 1 hour, and filtered. The solid was washed with 4X25 ml dioxane.

The filtrate and combined washings were concentrated to dryness in vacuo and the residue was dissolved in 120 ml absolute ethanol. Treatment with ethanolic hydrogen chloride gave in three crops 34.2 g (47 percent) of the product, m.p. l54180.

Purification was effected by recrystallization from absolute and subsequent vacuum sublimation at 220-230 (0.2 mm), m.p. 206-208.

Anal. Calcd. for C, H NO.HCI.%H O: C, 68.56; H, 6.62; N, 5.00; E 0, 1.61. Found: C, 68.88; H, 6.62; N, 5.01 H O, 1.48.

B. 6,6a,7,l lb-Tetrahydro-SH-indeno c]isoquinoline Hydrochloride To 31 1 g polyphosphoric acid was added 20 g (0.073 mole) of A. The mixture was stirred and heated at 95-l00 on a steam bath for 18 hours and poured into 2,000 g iced water. The mixture was cooled, 392 g KOH was added over 45 min to pH 10, and the alkaline material was extracted with 500 ml and 250 ml portions of CHCI The combined extract solutions were washed with 300 ml H O, dried (MgSO and concentrated to dryness in vacuo to give 12.0 g of an oil. The oil was dissolved in 35 ml absolute ethanol and 20 ml ethanolic hydrogen chloride was added. Upon cooling there was obtained 10.0 g (55 percent) of the product, m.p. 247260. Further recrystallization from absolute ethanol gave an analytical sample, m.p. 279 -284.

Anal. Calcd. for C H NHCI: C, 74.55; H, 6.26, N, 5.44. Found: C, 74.58; H, 6.45; N, 5.40.

, What is claimed is:

1 6,6a,7, l lb-tetrahydro-SH-indeno c]isoquinoline hydrochloride. 

1. 6,6A,7,11B-TETRAHYDRO-5H-INDENO(2,1-C)ISOQUINOLINE HYDROCHLORIDE. 